Show Notes

Tyler Post loved his career in education. As a former middle school teacher and principal, he was passionate about the work. But he also found the administrative side to be a constant grind of "reacting to issues" and "putting out fires," which ultimately "takes a toll." The pandemic was the final push he needed to seek a change. In this episode, Tyler shares his incredibly intentional, year-long transition out of the school building, which he navigated with the help of a career coach. He explains why he was drawn to sales—a field he loves because, unlike the "murky" metrics of education, his performance is "clear cut" and "defined by the numbers."

• A "Blind Spot" in School Data: Tyler explains his company, CrowdComfort, a technology platform that provides robust, real-time data for school facilities and custodial operations—a "blind spot" in most districts.
• From Teacher to Principal: Tyler shares his journey from teaching middle school social studies (and loving the "awkward" age) to becoming a principal, and how his background helps him understand the "deep, broad understanding" of how schools operate.
• Why He Left Administration: He gets candid about the "toll" of administrative life, the desire for better work-life balance, and the financial realities of working in education.
• The Appeal of Sales: Why did he choose sales? Tyler explains his competitive nature and the appeal of a job "defined by the numbers," a stark contrast to the "murky and challenging" task of measuring a teacher's impact.
• Advice: Be Deliberate: Tyler's number one tip for educators is to "be deliberate" and not just jump at the first opportunity. He advocates for a slow, introspective process and networking to find the right fit.

Episode Article

Tyler Post was a dedicated middle school teacher and principal who loved his work. He was passionate about the "awkward" but pivotal middle school years and thrived on helping students navigate that crucial time. But as he moved into administration, he found his days were consumed by "reacting to issues" and "putting out fires." He shared that while the role was satisfying, it's a grind that, over time, "takes a toll." The intense pressure of the pandemic was the final catalyst that made him realize it was time for a change.

But Tyler's transition wasn't a sudden leap. It was an incredibly intentional process. He worked with a career coach for a full year, "laying the groundwork" and doing the deep "introspection" required to figure out what skills he had and, more importantly, what he truly wanted in his next chapter. This deliberate process led him to a field he hadn't originally considered: sales.

What drew a school principal to sales? For Tyler, it was all about clarity. He explained that in education, measuring your impact is "murky and challenging." You're making a difference, but it's hard to quantify, and you often don't see the results for years. In sales, he was drawn to the fact that his performance is "defined by the numbers." He found this "clear cut" accountability, combined with his naturally competitive spirit, to be a refreshing new challenge.

Today, Tyler is an Account Executive at CrowdComfort, a company that provides data to school facilities and custodial teams. It's a role that perfectly leverages his background as a principal, giving him a "deeper, broader understanding" of the problems he's helping to solve. His advice for teachers considering a similar move is born from his own experience: "Be deliberate." Don't just jump at the first opportunity. Take the time to network, reflect, and find the role that truly aligns with your skills and what you've enjoyed most about your career in education.